Unsaturation Between The 4- And 5-positions (e.g., 21-thiol Prednisones, 21 Thio Cortisones, Etc.) Patents (Class 552/581)
  • Patent number: 8586770
    Abstract: The invention relates to methods to manipulate stem cells in vivo and in vitro to treat, e.g., a condition where cell or tissue repair is needed.
    Type: Grant
    Filed: February 18, 2011
    Date of Patent: November 19, 2013
    Assignee: Harbor Therapeutics, Inc.
    Inventor: James M. Frincke
  • Publication number: 20110262368
    Abstract: The present invention provides compounds of Formula (VII) and 11-keto analogs thereof, and pharmaceutically acceptable salts, solvates, esters, prodrugs, tautomers, and isomers of said compounds and said 11-keto analogs, having the general structure formula (VII): wherein L, R1, R2, R3, R4, and R5 are selected independently of each other and as defined herein. Also provided are pharmaceutical compositions, methods of preparing, and methods of using such compounds in the treatment and prophylaxis of a wide range of immune, autoimmune, and inflammatory diseases and conditions. The novel compounds of the present invention possess useful pharmacological activity while having unexpectedly low systemic activity. Thus, the compounds of the invention represent a safer alternative to those known glucocorticoids which have poor side-effect profiles.
    Type: Application
    Filed: December 18, 2008
    Publication date: October 27, 2011
    Applicant: Schering Corporation
    Inventors: John C. Anthes, Kevin D. McCormick, John A. Hey, Robert G. Aslanian, Purakkattle J. Biju, Michael Y. Berlin, Daniel M. Solomon, Philippa H. Solomon, Hongwu Yang, Yeon-Hee Lim, Yoon Joo Lee, Rema Danielle Bitar
  • Patent number: 7829555
    Abstract: The invention provides a method of targeting a drug to areas of hypoxic and/or ischemic tissue within the body in which the desired drug species is linked to a non-cytotoxic bioreductive carrier. Also provided by the invention are novel bioreductive conjugates comprising a non-cytotoxic bioreductive moiety with linked-thereto at least one therapeutic agent. The compounds of the invention are particularly suitable for the treatment of rheumatoid arthritis and other arthritic conditions, diabetes, atherosclerosis, stroke, sepsis, Alzheimer's disease and other neurological disorders, cancer, kidney disease, digestive diseases, liver disease, chronic periodontitis or ischemia following tissue transplantation.
    Type: Grant
    Filed: February 13, 1998
    Date of Patent: November 9, 2010
    Assignee: The University of Manchester
    Inventors: David Blake, Declan Naughton, Ged Adams, Margaret Adams, legal representative, Ian Stratford, Christopher Morris, Mohammed Jaffar, Matthew Naylor
  • Publication number: 20100247439
    Abstract: Provided are dendritic nano-antioxidant compounds according to Formula I, which may further comprise active agents covalently or non-covalently attached. Further provided are compositions comprising the disclosed compounds. Also disclosed are cosmetic compositions and dietary supplements comprising the compounds according to Formula I. The invention additionally provides methods of reducing free radicals or oxidative stress in a cell, a method of treating a subject, and a method of treating a condition comprising administering the compounds according to Formula I.
    Type: Application
    Filed: March 29, 2010
    Publication date: September 30, 2010
    Inventor: Choon Young Lee
  • Patent number: 5750745
    Abstract: Described is a process for the regioselective dehydration of 11-hydroxy steroids using PCl.sub.5, PCl.sub.3, POCl.sub.3 or either SO.sub.2 Cl.sub.2 and imidazole, or PPh.sub.3 and CCl.sub.4. The disclosed process selectively forms .DELTA..sup.9,11 steroids from either 11-.alpha.- or 11-.beta.-hydroxy steroids, and can also be used for the one-step conversion of 11,21 -dihydroxy steroids to 21-chloro-.DELTA..sup.9,11 steroids. Also disclosed are processes for the regioselective conversion of 11-.beta.-chloro steroids to .DELTA..sup.9,11 steroids, and for regioselectively converting an 11,17,21-trihydroxy streoid to a 21-chloro-11,17-dihydroxy steroid.
    Type: Grant
    Filed: November 18, 1996
    Date of Patent: May 12, 1998
    Assignee: Schering Corporation
    Inventors: Xiaoyong Fu, Tiruvettipuram K. Thiruvengadam, Chou-Hong Tann, Junning Lee, Cesar Colon
  • Patent number: 5710293
    Abstract: The present invention relates to a method of using a perchloric acid catalyzed reaction to make acyl derivatives of norprogesterone compounds and, in particular, 16-methylene-17.alpha.-hydroxy-19-norpregn-4-ene-3,20-dione.
    Type: Grant
    Filed: October 13, 1995
    Date of Patent: January 20, 1998
    Assignee: The Population Council, Center for Biomedical Research
    Inventor: Fang Li
  • Patent number: 5707984
    Abstract: Disclosed are steroid nitrite/nitrate ester derivatives of formula I: ##STR1## wherein, the substituents are as defined in the specification and their use in the treatment of inflammatory diseases.
    Type: Grant
    Filed: December 8, 1995
    Date of Patent: January 13, 1998
    Assignee: G. D. Searle & Co.
    Inventors: Foe S. Tjoeng, Mark G. Currie, Mark E. Zupec
  • Patent number: 5702702
    Abstract: The invention provides a modified human cytotoxic T cell line, which is characterized by dual activity in vitro and in vivo against malignant cells and virus-infected cells. Also provided are effective and safe methods for use of the modified cells in adoptive therapy of cancer and untreatable vital diseases in MHC-mismatched recipients, and in marrow purging to achieve complete eradication of residual tumor cells from marrows of patients with leukemia and other types of cancer. Also provided are effective and safe methods for use of the cytokine stimulated, irradiated TALL-104 cells in the manufacture of a veterinary composition for adoptive therapy of canine and feline malignancies.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: December 30, 1997
    Assignee: The Wistar Institute of Anatomy and Biology
    Inventors: Daniela Santoli, Giovanni Rovera, Alessandra Cesano
  • Patent number: 5602248
    Abstract: Disclosed is a process for producing a compound of the formula: ##STR1## by reacting a compound of the formula: ##STR2## with: (1) a chlorinating reagent selected from an N-chloroimide or an N-chloroamide; (2) an anhydrous strong acid selected from orthophosphoric acid, alkylsulfonic acids, fluoroalkylsulfonic acids or arylsulfonic acids; and (3) anhydrous dimethyl formamide; at a temperature within the range of about -78.degree. to about 0.degree. C., under anhydrous conditions under an inert atmosphere.
    Type: Grant
    Filed: March 16, 1995
    Date of Patent: February 11, 1997
    Assignee: Schering Corporation
    Inventors: Richard W. Draper, Eugene J. Vater
  • Patent number: 5412091
    Abstract: A compound of the formula ##STR1## in which ##STR2## is either a 3-keto-.DELTA.4-system or a 3-keto -.DELTA.1,4-system or a 3-OR.sub.4 - .DELTA.5-system in which R.sub.4 is hydrogen or a protector group of hydroxy, R is methyl --CH.sub.2 OH or --CH.sub.2 OR', in which R' is a protector group of hydroxy, R.sub.1 and R'.sub.1 are individually selected from the group consisting of methyl, a branched alkyl not possessing hydrogen in the .beta. position of 5 to 8 carbon atoms, aryl of up to 10 carbon atoms, heteroaryl of up to 10 carbon atoms and at least one heteroatom chosen from nitrogen, sulfur and oxygen and benzyl, n and m, are individually numbers 0 or 1, R.sub.2 and R.sub.3 are hydrogen or R.sub.2 is fluorine and R.sub.3 is formyloxy or acetyloxy and the dotted lines in position 9(11) indicate the optional presence of a second bond which is useful for the preparation of compounds of formula A.
    Type: Grant
    Filed: July 1, 1993
    Date of Patent: May 2, 1995
    Assignee: Roussel Uclaf
    Inventors: Jean Boivin, Christine Chauvet, Samir Zard
  • Patent number: 5352808
    Abstract: A process for the preparation of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms optionally substituted by halogen or a nitrogen or oxygen function and alkenyl and alkynyl of 2 to 4 carbon atoms, R.sub.2 is alkyl of 1 to 4 carbon atoms and the A, B, C and D rings are optionally substituted by at least one member of the group consisting of optionally protected --OH or .dbd.0, halogen, alkyl and alkoxy of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms comprising reacting a compound of the formula ##STR2## wherein R.sub.1 and R.sub.2 and the A, B, C and D rings are defined as above with an oxidizing agent in the presence of water and an at least partially water-miscible solvent to obtain a compound of the formula ##STR3## wherein R.sub.1 and R.sub.
    Type: Grant
    Filed: November 5, 1992
    Date of Patent: October 4, 1994
    Assignee: Roussel Uclaf
    Inventors: Jean Buendia, Michel Vivat
  • Patent number: 5159091
    Abstract: A process for preparing 21-desoxyprednisolone 17-esters of formula (IV) is disclosed. ##STR1## The process comprises reacting a prednisolone 17.alpha.,21-cyclic orthoester with an acid in a 40-60% lower alcohol solution to produce a prednisolone 17-ester, sulfonylating the prednisolone 17-ester into a prednisolone 17-ester 21-sulfonate, and reacting the sulfonate with an alkali metal iodide in methyl ethyl ketone in the presence of a lower fatty acid to produce the compound of formula (IV). The process ensures economical industrial production of high purity 21-desoxyprednisolone 17-esters, an excellent local anti-inflammatory medicine, in a high yield by simple procedures.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: October 27, 1992
    Assignee: SS Pharmaceutical Co., Ltd.
    Inventors: Tadatoshi Kuriyama, Masaki Ogawa, Susumu Sato, Naokata Taido, Tadayuki Kuraishi
  • Patent number: 5116829
    Abstract: A 21-substituted steroid compound is disclosed. The compound has a structure of formula (I), ##STR1## wherein R.sup.1 is a hydrogen atom, a lower alkyl, lower alkenyl, lower alkoxy, or phenyl group, R.sup.2 is a hydroxyl group or an acyloxy group having 1-6 carbon atoms, R.sup.3 is a hydrogen atom or a lower alkyl group, or R.sup.2 and R.sup.3 may together form a lower alkylidenedioxy group, X.sup.1 and X.sup.2 may be the same or different and individually represents a hydrogen atom or a halogen atom, Y.sup.1 and Y.sup.2 may be the same or different and individually represents a methylene group or a sulfur atom, Z is a sulfur atom or an imino group, the wave line means that the configuration of R.sup.3 may be of either .alpha. or .beta., and dotted line between the 1 and 2 position means that the bond may be the double bond.
    Type: Grant
    Filed: April 10, 1991
    Date of Patent: May 26, 1992
    Assignee: Kao Corporation
    Inventors: Kimihiko Hori, Yasuto Suzuki, Tomoki Morioka, Shigeru Moriwaki, Osamu Hirota, Shuichi Tsuchiya
  • Patent number: 5064822
    Abstract: Novel 3-keto-19-nor-.DELTA..sup.4,9 -steroids of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of naphthyl, phenylphenyl, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms optionally containing additional unsaturations, phenoxy, furyl, cycloalkyl of 3 to 6 carbon atoms, thienyl optionally substituted with at least one member of the group consisting of halogen and alkyl and haloalkyl of 1 to 6 carbon atoms and phenyl optionally substituted with at least one member of the group consisting of --OH, halogen, --CF.sub.3, alkyl and alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, phenoxy and alkylthio of 1 to 6 carbon atoms optionally oxidized to the sulfoxide or sulfone, R.sub.2 is selected from the group consisting of methyl and ethyl, R.sub.
    Type: Grant
    Filed: November 16, 1989
    Date of Patent: November 12, 1991
    Assignee: Roussel Uclaf
    Inventors: Daniel Philibert, Jean G. Teutsch, Germain Costerousse, Roger Deraedt
  • Patent number: 5063222
    Abstract: Steroid derivatives represented by formula (I) are disclosed. ##STR1## wherein R is a hydrogen atom, a halogen atom, a hydroxy group, or a group --OCOR.sub.1, wherein R.sub.1 is a linear or branched alkyl group which may be substituted by a halogen atom or a cycloalkyl group, a cycloalkyl group, or an aryl group. The compounds are useful for curing or alleviating inflammation or rheumatism.
    Type: Grant
    Filed: April 13, 1990
    Date of Patent: November 5, 1991
    Assignee: SS Pharmaceutical Co., Ltd.
    Inventors: Teruo Komoto, Junji Okawa, Yoichiro Ogawa, Susumu Sato, Naokata Taido, Tadayuki Kuraishi
  • Patent number: 4921638
    Abstract: The invention is the compound 17.beta.-cyano-9.alpha., 17.alpha.-dihydroxyandrost-4-en-3-one (I) which is particularly useful as an intermediate in the production of the 17.alpha.-halo silyl ethers (II).
    Type: Grant
    Filed: October 3, 1988
    Date of Patent: May 1, 1990
    Assignee: The Upjohn Company
    Inventors: Douglas A. Livingston, Bruce A. Pearlman, Scott Denmark, Joel E. Huber
  • Patent number: 4913852
    Abstract: Compounds obtained from the associative synthesis of sulfur-containing or sulfur-free amino acids with derivatives of .DELTA.-4-pregnene-3,20-dione or with derivatives of .DELTA.-1,4-pregnadiene-3,20-dione of the general formulas (I), (II) and (III), having glucocorticoidal and anti-inflammatory properties have been prepared and tested. Pharmaceutical compositions, medicaments containing them as well as their applications are claimed, particularly in the cutaneous and ophthalmic fields.
    Type: Grant
    Filed: February 24, 1988
    Date of Patent: April 3, 1990
    Inventors: Catherine Milioni, Constantin Efthyimiopoulos, Bernard Koch, Louis Jung, Jean Jung